Alicyclic bifunctional compounds and processes for their preparation

Abstract

The invention provides an alicyclic bifunctional compound represented by the formula ##STR1## wherein R is a carboxyl group, a lower alkoxycarbonyl group or a hydroxymethyl group and n is 0 or 1.

What we claim is: 
     
       1. A process for preparing an alicyclic cis-dicarboxylic acid represented by the formula ##STR11## the process comprising subjecting to oxidative cleavage reaction the double bond of an alicyclic monoolefin represented by the formula ##STR12## wherein n is 1. 
     
     
       2. The process according to claim 1 wherein the oxidative cleavage reaction is conducted under acidic conditions using a permanganate as an oxidizing agent. 
     
     
       3. A process for preparing an alicyclic trans-dicarboxylic acid represented by the formula ##STR13## the process comprising the steps of: esterifying the alicyclic cis-dicarboxylic acid recited in claim 1: isomerizing the resulting alicyclic cis-dicarboxylic diester ##STR14##  into a trans form; and hydrolyzing the trans form. 
     
     
       4. The process according to claim 3 wherein the isomerization is effected using a metal alkoxide as a catalyst. 
     
     
       5. A process for preparing an alicyclic cis-dicarboxylic diester represented by the formula ##STR15## wherein R' is a low alkyl group having 1 to 4 carbon atoms, the process comprising ##STR16## esterifying the alicyclic cis-dicarboxylic acid recited in claim 8. 
     
     
       6. A process for preparing an alicyclic trans-dicarboxylic diester represented by the formula ##STR17## wherein R' is a lower alkyl group having 1 to 4 carbon atoms, the process comprising isomerizing the alicyclic cis-dicarboxylic diester recited in claim 5 ##STR18## into a trans form. 
     
     
       7. The process according to claim 6 wherein the isomerization is effected using a metal alkoxide as a catalyst. 
     
     
       8. A process for preparing an alicyclic cis-diol represented by the formula ##STR19## wherein n is 1, the process comprising ##STR20## reducing the cis-dicarboxylic diester recited in claim 5. 
     
     
       9. The process according to claim 8 where the reduction reaction is effected through catalytic hydrogenation in the presence of a hydrogenation catalyst. 
     
     
       10. A process for preparing an alicyclic trans-diol represented by the formula ##STR21## wherein n is 1, the process comprising the steps of; ##STR22## isomerizing the cis-dicarboxylic diester recited in claim 5 into a trans form; and reducing the trans form.   
     
     
       11. The process according to claim 10 where the isomerization reaction is effected in the presence of a metal alkoxide as a catalyst, and the reduction reaction is effected through catalytic hydrogenation in the presence of a hydrogenation catalyst. 
     
     
       12. A process for preparing an alicyclic cis-diol represented by the formula ##STR23## where n is 0, said process comprising the steps of: cleaving by oxidation the double bond of an alicyclic monoolefin represented by the formula ##STR24##  wherein n is 0, to give a cis-dicarboxylic acid; esterifying said acid into a cis-dicarboxylic diester; and reducing said diester. 
     
     
       13. The process according to claim 12, where the oxidative cleavage reaction is conducted under acidic conditions using a permanganate as an oxidizing agent and the reduction reaction is effected through catalytic hydrogenation in the presence of a hydrogenation catalyst. 
     
     
       14. A process for preparing an alicyclic trans-diol represented by the formula ##STR25## wherein n is 0, the process comprising; cleaving by oxidation the double bond of an alicyclic monoolefin represented by the formula ##STR26##  where n is 0, to give a cis-dicarbxylic acid; esterifying said acid into a cis-dicarboxylic diester; isomerizing said diester into a trans form; and   reducing said trans form.   
     
     
       15. The process according to claim 14, where the oxidative cleavage reaction is conducted under acidic conditions using a permanganate as an oxidizing agent, the isomerization reaction is effected in the presence of a metal alkoxide as a catalyst, and the reduction reaction is effected through catalytic hydrogenation in the presence of a hydrogenation catalyst.